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Strategy·May 11, 2026·6 min read

What nobody tells you before you hire someone to build your website

After 20 years in this industry, a few things about how web projects go wrong — and what to ask before you sign anything.

What nobody tells you before you hire someone to build your website

Most web design content is written by agencies trying to get hired. Which means it tells you what agencies want you to know, not necessarily what you need to know. After twenty years in this industry — building sites, running agencies, watching projects go sideways — here are the things that rarely come up until after something has gone wrong.

The person who sells you the project is usually not the person who builds it

At most agencies of any real size, the sales process and the production process involve different people. The senior strategist or account lead who understood your business, asked good questions, and made you feel confident — they go back to selling once the contract is signed. Your project moves to a production team working from a brief.

This isn’t a scandal. It’s just how agencies manage capacity. But it means the relationship you bought isn’t always the relationship you get. The questions to ask before signing: who specifically will be working on my project, what is their experience level, and will I have direct access to them?

At a boutique or with an independent, the person you talked to is usually the person doing the work. That’s the tradeoff for scale — you get continuity but not a bench.

Revision rounds are not unlimited, and scope creep is real

Most web design contracts specify a number of revision rounds. What counts as a revision is often undefined, which creates friction when a client asks for something the agency considers out of scope.

This isn’t about bad faith on either side — it’s about two parties having different mental models of what the project includes. The client thinks “we’re still in the design phase, of course I can change my mind about the homepage.” The agency is tracking hours against a fixed budget and every change is real work.

Before signing, understand exactly what’s included in each phase, what triggers a change order, and what the process is for requesting work outside the original scope. A good agency will walk you through this without you having to ask. If they’re vague about it, that’s information.

Launch is not the end of the project — it’s where the real costs begin

The sticker price of a website is the build cost. The actual cost of a website includes hosting, security monitoring, software updates, plugin maintenance, content updates, and eventual redesign. None of those are optional if you want the site to keep working.

A lot of small businesses make the mistake of treating their website like a one-time purchase. They pay for the build, launch it, and assume it will run itself. Then eighteen months later a plugin conflict breaks the site, or a WordPress core update causes display issues, or a security vulnerability gets exploited, and they’re paying emergency rates to fix something that routine maintenance would have prevented.

Ask any agency or developer you’re considering: what does ongoing maintenance look like, what does it cost, and what happens if I don’t do it? The answer tells you a lot about how they think about the work.

“We’ll train you to update it yourself” often doesn’t work out

Many agencies offer a training session at the end of a project so clients can manage their own content. The theory is sound. In practice, most small business owners don’t update their own sites — not because they’re incapable, but because they’re busy running their businesses and the site updates don’t get prioritized.

If self-managing your content is part of your plan, be honest with yourself about whether that’s actually how your bandwidth works. A site that nobody updates is a site that quietly gets worse over time — outdated services, old team photos, events that passed six months ago, copy that no longer reflects the business.

Some clients genuinely do maintain their own sites well. They tend to have someone on staff whose job includes it. If that’s not your situation, budget for ongoing support rather than planning to handle it yourself and discovering later that you didn’t.

Platform loyalty is a red flag

An agency that leads every conversation with the same platform recommendation — regardless of what you’ve told them about your business — is telling you something about how they work. They’re not diagnosing your problem and recommending a solution. They’re selling you what they know how to build.

WordPress is the right answer for a lot of projects. So is a modern headless stack. So, occasionally, is something simpler. The right answer depends on your content model, your team’s capacity, your growth trajectory, and what you’re actually trying to accomplish. An agency that’s figured all that out before your first conversation didn’t figure it out — they assumed it.

The question to ask: have you worked with clients who ended up not needing what you initially recommended? What happened? A good answer involves a real example. A bad answer involves deflection.

Price is not the best proxy for quality

Web design pricing varies enormously and correlates imperfectly with outcomes. A $15,000 agency project can produce a mediocre site. A $5,000 boutique project can produce something excellent. The variables that actually predict quality — the experience of the person doing the work, their process for understanding your business, their track record with similar projects — don’t map neatly onto price.

That said, price is also not irrelevant. Very low prices usually mean very fast work, which means less time spent understanding your business before building. The floor for a genuinely custom, well-built site from someone experienced enough to be worth hiring has gone up over the years, not down.

The right question isn’t “how much does this cost” — it’s “what am I getting for this investment, and what’s the evidence that this person can deliver it?” Ask to see work. Ask to talk to past clients. Ask what they would do differently on a project that didn’t go as well as they hoped. The answers tell you more than the price does.

The best web projects feel like a conversation, not a transaction

The projects that go well — where the site does what it was supposed to do and the client feels good about the investment — almost always have one thing in common: the client and the builder were genuinely communicating throughout, not just exchanging deliverables.

That requires effort on both sides. The client has to be willing to articulate their business, share context about what’s changed, and give honest feedback rather than vague approval. The builder has to ask real questions, push back when something isn’t right, and treat the client’s business goals as the actual deliverable — not the Figma file.

If a sales process feels like being processed rather than understood, the project probably will too.

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